Rebirth and Growing Pains (March-November 2000)
Okay, so now I am back to being a woman from time to time. Not always the easiest thing…
March 22, 2000:
Dear Diary:
…I've been taking care of me, too. I have a few outfits courtesy of local thrift shops - not anything
too big or flashy. My knees are cracked from the dry heat; and the leftover cream is being applied
twice a day. At least I'm not on my knees in front of the computer anymore. That helps! I'm also
doing more housework now, and I'm allowing myself to discover who I really am.
Luv `n hugs always,
Jayne
April 15, 2000:
Dear Diary:
I was busy today! A full load of cleaning, cooking…I feel so domestic when I can do these things!
I have a few new things, but not much of a chance to wear them. I just wish I wasn't so tired!
Luv `n hugs always,
Jayne
May 24, 2000:
Dear Diary:
I went shopping today. I got some earrings, and an exercise bra and panties. I need to lose a few
pounds-but what girl doesn't? Still, I'm excited. More clothes, and maybe a chance to wear them!
…I am starting to understand who I am as a result. Now, if I can just find a name for what it is…
Luv `n hugs always,
Jayne
You must understand…I had not heard of transgenderism or Gender Dysphoria yet. I knew I was
not a transvestite, but also knew I was far more than a cross dresser…I had so much to learn and
didn't know it!
Sex, while interesting, has never really been the focus of my progression towards womanhood:
May 30, 2000:
Dear Diary:
Sex. Sometimes I think it is so overrated. I mean, I like to have a good cock now and then, but I'm
still not so sure that it's all it is cracked up to be. Like the last time I was taken by Dan (clear back on
March 9), I told him to be careful and even so, I still bled for an hour afterward (Not much, just
enough to be annoying). I've enjoyed having cocks to suck, but want more from a relationship than
sex. I want to be cuddled and kissed. I'd love to be romanced, dined, danced with…as a woman, I
crave these things.
…The next time I do him, though, 2 things: one, gentle means gentle! And the other: Nobody calls me
a bitch anything (much less bitch boy). I'll slap him for sure if he does!
(Though he might like it…)
Luv `n hugs always,
Jayne
The good news is, about this time, I got a job. Finally. That meant that I could start to afford
some better things now! J
While interesting, sex , on the other hand, is what carries hope with it every so often…
July 22, 2000:
Dear Diary:
We are going to this week long seminar, and I for one am looking forward to it. I've planned on
packing most of my femme stuff-in hopes I get lucky with my roommate. So, I got some nails, makeup,
and hose. I've already figured out I need about a quarter of my suitcase for my female things; but that
will not be a problem. I'm hoping to be able to wear panties for the week, and maybe a bra, too! Also-I'd better
take the extra nail tabs, too-I might just need them on a regular basis!
I'm starting to wonder how to hide all this stuff-I don't think it's an issue yet-but it will be quite
soon. What's a girl to do?
Luv `n hugs always,
Jayne
As time goes by, we all start to wonder about boobs. Without even thinking of the possible
ramifications, I just started looking around for something…
July 27, 2000:
Dear Diary:
This is it. I have another pair of panties, some fat-burner, a new can of mousse, some new soap…and
some soy-estrogen called New Phase. I have had boobs for quite awhile, but if I can start to lose some pounds
and get some help with my boobs, I'll look better than I do now. The fat-burner might help
while I'm out at seminar. Something's got to help out here…after all, it's my body…
Luv `n hugs always,
Jayne
Of course, just because we have hope, does not mean that it is fulfilled…
And, just because we think something is safe does not make it so!
July 30, 2000:
Dear Diary:
UGH! My room here is totally awash in testosterone! Not only is my roommate straight, he's ugly
and a heavy drinker, too! Well…I'll just have to work around that. Wore a bra and panties to the
session tonight. I almost got caught without a top on-which would show strap marks from my bra!
Guess I'll have to be more careful. I intend to keep on the lookout, but it's just my luck to be in a
"straight line" this week. Which means after all that, I won't get to do much at all. (sigh…) It's
probably better this way…but I'm still sorta disappointed. After all…this is supposed to be a
vacation!
Luv `n hugs always,
Jayne
Even when you are out of your comfort zone, however, you can learn if you will take the time to do so.
Not all learning comes from book--or the `net. You just have to listen…and take the time to apply
what you learn. This is where we start to do our nails, and learn of a new term: Transgender.
August 2, 2000:
Dear Diary:
I've enjoyed being in a bra and panties so far, though my straps need adjusting every so often, and I
have to change my pads right after dinner. I get away with the bra…no bulges where there shouldn't
be, and my boobs aren't that pronounced…I met a guy who's a professional beautician. He says I
should file my nails-so tonight, I did. They have a more feminine look to them, and I guess I'm going
to have to get a file I can keep with me. After all, a girl's got to look good, even when she's a boy.
Which reminds me-I found out that what I am is "Transgendered". By using the web here, I've done
enough to figure that much out. I will do more later, to be sure.
Luv `n hugs always,
Jayne
It is quite one thing to come out to a trusted friend or two. It is another thing to virtually announce
it to the world, regardless of how one does it…
August 10, 2000:
Dear Diary:
…I registered a new e-mail address: Jayne83@gay.com (So I can e-mail Dan and flirt, plus any other
TG's I find). I'm not really looking for a new relationship, but I am looking for others like me. And the
only way to do that is to get out and go looking. After all-it's not pretty being easy!
Luv `n hugs always,
Jayne
Makeup. For some of us, it's a luxury. For others, a necessity. But for all of us, we had to learn how to
apply it…sometimes the hard way.
August 29, 2000:
Dear Diary:
The makeup trials went well-I applied it all twice, so as to get the hang of it. Saturday night
(the 26th) I had to get a darker lipstick and blusher; tonight was an eyebrow pencil. I still need
to work at it, but…I can only do so much in a four hour sprint. I honestly don't know how a
person can just "toss on" makeup--I suppose it just takes practice!
Luv `n hugs always,
Jayne
When we get a chance to really dress up, the chance to "play" for a few days--the chance to dress up
and be the women we really are for a time-it is always an exciting time. This is our chance to dream.
These are the entries of one such time…
September 5, 2000:
Dear Diary:
I am so excited about the next few days I can hardly stand it! I had to buy a new pair of panties; a
fellow down at the shop got a bit rough-ripped them badly down a seam. (It never ceases to amaze me
how rough a man can be when he wants his cock sucked.) Also-bought the vanilla trio (soap, lotion,
and body spray) and some vanilla votives, for setting a mood.
I'll be keeping tabs on the "Holiday En Femme" as it happens-I don't want to lose a single, precious moment
that I don't have to lose. This will be a very special time-a chance to learn more about who
I am as a woman.
Luv `n hugs always,
Jayne
September 7, 2000:
Dear Diary:
MMMMmmmm…what a day! After quietly snagging my nail polish, I went shopping. Bought femme
razors, fat-burner, femme anti-perspirant, a new box of pads(I'll be in panties for four days, after all),
a disposable 35mm camera for pictures, a satin pillowcase, and breakfast. Got to work, changed into
the panties (it felt soooo good!), did my fingernails in clear polish (2 coats)-and then realized I
didn't have lunch! So…I did lunch with the S.O. and her dad. I was a little conscious about my nails,
but played it down well. After work, I went home, stripped the clear coat off my toes, and put a fresh
coat of colored polish down. After the second coat dried, I put my black lace bra on, a t-shirt, grabbed
my stuff and took care of some late business, leaving with enough time to catch Dan. I changed into my
lycra top enroute, and put a jacket on over that, so I passed for butch. We went to the shop, and there I
had a most erotic experience. This guy started kissing me through a glory hole, and eventually we were
in the same booth. Kissing, sucking, feeling, fondling-it was sooo intense! We both got close, but he was
shooting blanks. After that, I finally got someone to come and vice versa. Dan was a little jealous of my
first, but got over it quickly. He introduced me to a friend, and when we finally parted, I swayedlike a
lady ought to. Came home, talked to the S.O., then did the building sweep. Changed into my blue
chemise and relaxed…Got this far, but it is getting so late, and tomorrow's another day.
Luv 'n hugs always,
Jayne
September 8, 2000:
Dear Diary:
Mmmm…I could get used to this kind of living very quickly. Woke up, did the work thing in panties
that I put on at home, drove in, came home-- Dan came over, I did some typing for him, then while
he showered, I changed into the black outfit. When he came out, I was all over him like white on rice.
I sucked on him for awhile, then he had me pump him. I'm really not into giving anal, but he likes it,
so….anyway, after that we went out and had some food at McD's. After the sweep, it was back into a
chemise (the pink one) to get this caught up. From here, I'm going to Gay.com & check out some TG
sites-there is some much I need to learn about this!
I hope Dan had a good time; I did-and his friend last night commented on my butt!
Now there's a first!
Luv `n hugs always,
Jayne
September 9, 2000:
Dear Diary:
MMmmmm…I need more days like today-got up, played on-line, went looking for wigs (gave up; none
looked good enough) took back the 35mm camera and exchanged it for a roll of film, then after dinner,
a nice, hot, luxurious bath and shower-then I started the photo shoot.
I had a ball!
I wore everything, used makeup, jewelry-the whole thing. I would have liked it better if someone
could have taken the pictures for me, but with a timer most of them should come out okay. I'm going
to develop them to disc; then I can crop them and touch them up so I look really pretty. Once I took the
makeup off, I redid my nails for church-then sat down to write this. I tried going back online, but
things are just too slow tonight.
In a way, I'm sad because tomorrow after church I have to go butch again-and I really don't want
to. I've enjoyed this time, maybe too much-but I hope to have a chance to do this again really soon.
Well, Diary, I guess I'd best get some sleep-tomorrow will be a very long but very short day.
Luv `n hugs always,
Jayne
September 10, 2000:
Dear Diary:
What a day-I did go to church today-in panties, a bra (the lacy white underwire one), nails in
clearcoat, lipgloss…I LOVED it! Came home, washed all my femme clothes, bought another set of
skirt/blouse hangers, a belt, and some more Soft `n Dry. (I need to find a way to use this more often
than my homme antiperspirant.) Got everything hung up, pulled the colored polish off the toes and
clearcoated them, pulled the polish off my fingernails (grudgingly), and made sure everything was
put away and looking like a man lived there. It made me very depressed to go butch again, but I
know I had to. I wish the S.O. would be more open and flexible, but I know she never will. Which is
really too bad, because I think she'd be more comfortable all the way around. (sigh….) Well-gotta go-
the morning comes too early!
Luv `n hugs always,
Jayne
Part of becoming a woman really does deal with what you wear…! In addition, I start down a new
avenue: bookwriting.
September 14, 2000:
Dear Diary:
I love being a woman!
In addition to getting another box of soy-estrogen, I bought a whole bunch of diet stuff, weights
and such. My pics were in, too-no sweat picking them up, and I got a large Soft `n Dri…and my very
first slip. I need one for under my skirts…yesterday I started writing a book called "The Weekend Woman".
It's kind of a how-to thing, so others like me who are starting out can have a basic refererence…
Luv `n hugs always,
Jayne
Some days, I, like you, have my dreams...
October 18, 2000:
Dear Diary:
…writing "The Weekend Woman" and this little journal is helping me with my dual nature-which is
good. I like the sense of peace I have now-if I could just dress around the S.O. , that would be great!
Luv `n hugs always,
Jayne
I run the risk of getting my S.O. pregnant at any time. This is what happens when I did, once.
Only one problem: How to be a Dad AND a Mom…!
October 26, 2000:
Dear Diary:
It's official: she's pregnant. I hope she's happy! I'm not sure she understands what she's in for. I know
I don't-and it is very scary in this dual nature….
Luv `n hugs always,
Jayne
As time goes by, we get bolder as we go. We start looking for ways to express our female side…even if it
means looking androgynous at first.
October 28, 2000:
Dear Diary:
…Today is a special day-I went out dressed in all-women's clothing (as much as possible) for the first
time. I was out all of a half-hour, but it felt so good to be a woman….I found a pair of jeans that fit me
just right (if you know what I mean!) and just had to try them out, along with a white bra and panties,
my blue lycra top and belt. It was WONDERFUL!
Luv `n hugs always,
Jayne
Another milestone, of sorts: do you remember your very first perfume? Not only do I remember it, but
I wear it often these days!
November 15, 2000:
Dear Diary:
I'm becoming more female-and more daring-as time goes by. I bought a little purse that fits inside my
pouch, and tonight bought my very first perfume: Vanilla Fields. I'll get to wear it some while the S.O. is
gone in a few weeks. It's the best birthday present she could give me, and she doesn't even know it-4+
days of femme time…I am taking advantage of all the time I can to be a woman. She has no idea!
Luv `n hugs always,
Jayne
Sometimes I get depressed. Bear in mind that I live two hours from anywhere, and while there are
professional transvestites in my area, it's not like I can call one and say, "Let's do lunch"….
November 30, 2000:
Dear Diary:
…I mean, it's not like I have a bunch of TG friends I can call and party with, or hang out with, or
whatever. Heck-I don't even have a lot of stright friends out here! (Sigh…)
Sometimes, I wonder what it's like to really be free. To not have to hide behind the mask of
respectability. To be able to go out & not care who sees me. To be accepted for who I am, not what I
could/should or can be. I can't do that here-too much fear of the unknown, too much hatred. Sasha
Devereaux is right: "There may not be swords"…but there is definite danger in being TG.
And that's really too bad, because I could offer so much more if I could be free to be me.
Luv `n hugs always,
Jayne
This is where I end this section of diary. December will be in the next section…this is a difficult section
for me to write. In the midst of my week while my S.O. is gone, she miscarried our first (and only) child.
And while there is a certain sense of relief (it makes it easier to be the way I am), it also carries
a certain sadness…of what might have been. Don't forget, ladies…I don't just have woman's boobs-I
also have a woman's heart. And it can be broken easily.